The Art of Asking—Boldly and Deeply

By Anonymous

“Be unabashedly curious.”

This was the mantra in a course I took last year that trained us to be mediators. Every position that a disputant takes has underlying interests. Every event has a history. Every facade has a face.

When I shared with my community last year that I struggled with same-sex attraction (SSA), my community reacted wonderfully. Many affirmed my honesty and courage, some hugged me (even the guys, which quelled my worst fears that they would be disgusted) and my closer friends told me they were proud of me (which meant more than you know—thank you).

A few months after that, nothing. No one asked me about my journey in this struggle, what it was like, where I am now. No one asked me where I saw God. It was as if I had never shared at all.

For that brief moment when I had come out to my community, I felt the love and warmth and connection. And then, I felt more isolated than ever before.


Everyone has a story to tell; sometimes, we just forget to ask for it.

In Forming Intentional Disciples, Sherry Weddell points out that Jesus “almost never gave a straight answer to a straight question. In the New Testament, Jesus asked 183 questions, gave 3 answers, and answered 307 questions with a question in return like a true rabbi.”

Consider the example of a person who keeps coming late for community events.

“Why are you always late?”

“I have family meals on Sundays.”

That could have been the end of the conversation. But imagine if someone was courageous enough to probe further.

“You can’t change your family meal timings arh?”

“I can, but actually, I also don’t like being around in community that much.”

There is tension now. Imagine if the response was curiosity instead, with a dose of insight.

“Why do you keep coming then if you don’t like it?”

“Because I promised God that I would come.”

And there, the door to a backstory opens. It is not a coincidence that the sentence beginning with “Ask…” ends with “… and the door will be opened for you.”

Sometimes, these doors present themselves under unexpected circumstances; our deepest conversations can arise from fortuitous musings.


As CS Lewis wrote: “There are no ordinary people. You have never talked to a mere mortal. Nations, cultures, arts, civilisations—these are mortal, and their life is to ours as the life of a gnat. But it is immortals whom we joke with, work with, marry, snub, and exploit—immortal horrors or everlasting splendours.”

And so Evangelii Gaudium exhorts us at [169] to practice the “art of accompaniment” which “teaches us to remove our sandals before the sacred ground of the other.”

We can learn much from Moses here. Moses had followed his curiosity about the burning bush, which led him to his conversation with God, and inevitably, to him asking: “What is [God’s] name?” (Ex 3:13) In reply, and in the most unequivocal declaration of holiness among all the other wonders that Moses witnessed at Mount Horeb, God reveals His Divine Name: “I am who I am.”

Thus have Christianity’s central questions always been about identity: Who am I? Whose am I? And at the heart of our faith is not a question that we ask, but a question that is asked of us: “Who do you say I am?” (Mt 16:15)

Apart from our apathy (which really reflects more about us than about the other person), there is another key reason why we do not ask: we fear rejection.  Sometimes, we are afraid of asking the wrong question, of offending the other person. How do I ask about his gay struggle? Wait, is ‘gay’ even the correct word to use? (No, it isn’t, but we get what you mean.) This is not something I can ever relate to, so how can I even try to understand?  

Other times, we are afraid of being seen as weak, bothersome, or nosy. “Why are you so interested in my story?” When I told a friend I’m generally curious, she retorted, “If you were my facilitator, I think I wouldn’t have liked you.”

More often though, we are simply afraid of the other person saying ‘no’. In my more neurotic days, I had asked my best friends whether they had placed me on the same pedestal that I had placed them on in my life. Their answer devastated me for months. As Amanda Palmer points out in The Art of Asking, it is easy to love passing strangers unconditionally, just as it is to ask them a survey question or for directions. It is much harder to ask and to risk being rejected by the people who matter most.


“But asking can hurt,” she writes. Amidst these fears, how do we then practice the art of asking? I propose seven ways.

One, dare to ask. I caught up with one of my community members recently. She is married. And somehow, we broached the topic of using Natural Family Planning (NFP). How do I, a guy who experiences SSA and has never even dated, even begin to ask a married woman about her bedroom practices?

Clumsily—that’s how. So I asked. And she shared. And I learned a whole new dimension of a couples’ journey.

Thus, even when—in fact, especially when—our life experiences are wholly different from the other person’s, we should ask. That is the only way we can thin the gap between the vast variances of our lives.

Two, be interested. Where curiosity leads, questions will follow, and doors will open.  And we should also certainly avoid presumptions. Leading questions—questions that presume or contain their own answers—are sterling counter-examples. You’re late because you’re not interested, right? You’re disruptive because you just want attention, isn’t it? 

That last leading question hits close to home. I once sat down with a kid who I felt was being disruptive and disconcerting in the way he was behaving. I tried to cross-examine him into realising that he was merely seeking attention and that he was causing more harm than good.

He caught on to me quickly and got really upset; and I felt terrible. My questions had been manipulative, I had talked down to him, and I had suggested that he was being self-serving when all that he was being was innocent. I apologised to him the next day, and before I could finish, he hugged me and said, “Aiya it doesn’t matter la.”

Everlasting splendours indeed!

Three, account for the individual’s uniqueness. This is a by-product of being interested: we become aware of and sensitive to the individual’s circumstances.  Prudence and precision give questions their potency. Case in point: Fr Jude’s perfectly timed “what stirs your heart?” was the hook that reeled at least two boys fresh out of army to the School of Witness this year.

Four, follow up. People do share parts of their lives—often deep, always real—with us, without us even asking. These are gifts.

But what do we do with them? We bury them in the ground. We assume that is all the individual is comfortable with sharing, so we refrain from asking further. Here is an audacious alternative: talk to the person about what he or she has shared. Like Jesus said, “to all those who have, more will be given” (Mt 25:29). We can follow up, ask questions, even pray for each other. If we are interested in them, then these should come naturally as well.

Five, be sincere, be open. When all else fails, awkward honesty will not.

Eventually, people did ask me about my SSA journey. The first few that did had no other contact with anyone else with similar struggles, so they stumbled over what to ask. They were so awkward that I felt bad for them, so I rescued them (after laughing at their discomfort) by sharing more on my own accord.

But a more immature me might have been offended by how maladroit they were. Or more childishly, I might have thought that their ignorance makes them unworthy to share in my struggle. Or I may just not have been ready to share any more than I already did. That leads to the next point.

Six, be prepared to accept a ‘no’—which is a corollary of being open. When we ask, we must allow the person the option not to answer, because that is their prerogative. Their life is theirs to share with us only if they wish to. “If we don’t allow for that no,” Palmer writes, “we’re not actually asking, we’re either begging or demanding.”

Seven, engage one-to-one. It is undeniably difficult to ask intimate questions in a group. After all, even Jesus spoke to the Samaritan woman at the well, in private. In these quiet spaces, some of my most spontaneous and interesting conversations arise.

And there we have it—seven tips to practice the art of asking. Any questions?

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